ChemInform Abstract: DIRECT SYNTHESIS OF α,β‐UNSATURATED NITRILES FROM ACETONITRILE AND CARBONYL COMPOUNDS: SURVEY, CROWN EFFECTS, AND EXPERIMENTAL CONDITIONS

DiBiase, Stephen A.; Lipisko, Bruce A.; Haag, Anthony P.; Wolak, Raymond A.; Gokel, George W.

doi:10.1002/chin.198014202

Cited by 4 publications

(4 citation statements)

References 1 publication

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“…Although this might seem an unlikely process, we have shown previously that under basic conditions, benzophenone and acetonitrile condense to form 2,2-diphenylacrylonitrile (17) in 84% yield.4 An alternative explanation of the formation of 17 is shown in eq 4-6. This mechanism seems consistent with Pb2CHCH2CN --BuOI<» Ph2CÍH2CN Ph2CCH2CN (4) . 02 PhCCH2CN --Ph2C(CH2CN)00• -Ph2C(CH2CN)OOH (5) CN literature proposals and, although more direct than the above, is not as simple and should be regarded as speculative.…”

Section: Resultssupporting

confidence: 83%

Crown cation complex effects. 10. Potassium tert-butoxide mediated penultimate oxidative hydrolysis of nitriles

DiBiase¹,

Wolak²,

Dishong³

et al. 1980

J. Org. Chem.

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Section: Resultssupporting

confidence: 83%

Crown cation complex effects. 10. Potassium tert-butoxide mediated penultimate oxidative hydrolysis of nitriles

DiBiase¹,

Wolak²,

Dishong³

et al. 1980

J. Org. Chem.

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“…Acetonitrile can undergo addition reactions with certain alcohols in the presence of concentrated acids . In the presence of strong bases, acetonitrile can be deprotonated to form the cyanomethide ion, which is reactive toward carbonyls and alcohols . The laboratory-generated OA extracts as well as extracts of field PM samples are expected to be neutral or weakly acidic .…”

Section: Discussionmentioning

confidence: 99%

The Effect of Solvent on the Analysis of Secondary Organic Aerosol Using Electrospray Ionization Mass Spectrometry

Bateman

Walser

Desyaterik

et al. 2008

Environ. Sci. Technol.

101

138

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This study examined the effect of solvent on the analysis of organic aerosol extracts using electrospray ionization mass spectrometry (ESI-MS). Secondary organic aerosol (SOA) produced by ozonation of d-limonene, as well as several organic molecules with functional groups typical for OA constituents, were extracted in methanol, d3-methanol, acetonitrile, and d3-acetonitrile to investigate the extent and relative rates of reactions between analyte and solvent. High resolution ESI-MS showed that reactions of carbonyls with methanol produce significant amounts of hemiacetals and acetals on time scales ranging from several minutes to several days, with the reaction rates increasing in acidified solutions. Carboxylic acid groups were observed to react with methanol resulting in the formation of esters. In contrast acetonitrile extracts showed no evidence of reactions with analyte molecules, suggesting that acetonitrile is the preferred solvent for SOA extraction. The use of solvent-analyte reactivity as a tool for the improved characterization of functional groups in complex organic mixtures was demonstrated. Direct comparison between mass spectra of the same SOA samples extracted in methanol versus acetonitrile was used to estimate the lower limits for the relative fractions of carbonyls (> or = 42%) and carboxylic acids (> or = 55%) in d-limonene SOA.

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“…IR spectra were obtained on a JASCO FT/IR-4100 spectrometer. Synthetic method for compounds 5 34 , 15 35 , 23 36 , 28 37 , 34 38 , S1 39 , S3 39 , S11 40 , S13 41 , S18 42 , S21 43 , S23 44 , S25 45 , S27 46 , S31 47 , S33 48 , S37 49 The mixture of S1 (169 mg, 1.02 mmol), (1,3-dioxolan-2-yl)methyltriphenylphosphonium bromide 651 mg, 1.52 mmol), K 2 CO 3 (208 mg, 1.50 mmol) and 18-crown-6 (6.38 mg, 0.0241 mmol) in toluene (10.0 mL) was stirred at 100 °C. After being stirred for 21 h at this temperature under Ar, the mixture was diluted with EtOAc.…”

Section: Methodsmentioning

confidence: 99%

Identification of Novel MR1 Ligands Derived from Herbal Medicines by MR1-Presentation Reporter Screening and Their Structure-Activity Relationship

Matsuoka

Hattori

Oishi

et al. 2022

Preprint

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Mucosal-associated invariant T (MAIT) cells are innate-like T cells that are modulated by ligands presented on MHC class I-related proteins (MR1). These cells have attracted attention as potential drug targets because of their involvement in the initial response to infection and various disorders. Herein, we have established the MR1-presentation reporter assay system employing split-luciferase, which enables the efficient exploration of MR1 ligands. Using our screening system, we identified herbal medicine-derived MR1 ligands, including coniferyl aldehyde, which have an ability to inhibit the MR1–MAIT cell axis. Coniferyl aldehyde comprises phenylpropanoids and is a novel motif for MR1 ligands. Further structure-activity relationship study revealed the key structural features of ligands required for MR1 recognition. These results will contribute to uncovering the mode of action of herbal medicines and their analogs, and to developing novel MAIT cell modulators.

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ChemInform Abstract: DIRECT SYNTHESIS OF α,β‐UNSATURATED NITRILES FROM ACETONITRILE AND CARBONYL COMPOUNDS: SURVEY, CROWN EFFECTS, AND EXPERIMENTAL CONDITIONS

Abstract: Oxo‐Verbindungen (I) reagieren mit den Anionen von Acetonitril in (II) über die Addukte (III) zu den substituierten Acetonitrilen (IV).

Cited by 4 publications

References 1 publication

Crown cation complex effects. 10. Potassium tert-butoxide mediated penultimate oxidative hydrolysis of nitriles

Crown cation complex effects. 10. Potassium tert-butoxide mediated penultimate oxidative hydrolysis of nitriles

The Effect of Solvent on the Analysis of Secondary Organic Aerosol Using Electrospray Ionization Mass Spectrometry

Identification of Novel MR1 Ligands Derived from Herbal Medicines by MR1-Presentation Reporter Screening and Their Structure-Activity Relationship

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